


Bliss

by rw_eaden



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Begging, Bisexual Dean Winchester, Bottom Dean, Bottom Dean Winchester/Top Sam Winchester, Brat Dean, Confident Sam, Dean's an asshole and can't stop being cocky so he sucks at roleplay, Early in Canon, First Time, Incest, Incest Kink, M/M, Mild D/s, Pansexual Sam Winchester, Plot What Plot/Porn Without Plot, Sexual Roleplay, Sibling Incest, Size Kink, Top Sam, Virginity Kink, tipsy sex, until he doesn't...
Language: English
Status: Completed
Published: 2017-06-04
Updated: 2017-06-04
Packaged: 2018-11-08 21:23:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11090187
Author URL: https://archiveofourown.org/users/rw_eaden/pseuds/rw_eaden
Summary: Dean's not totally sure how they got here, but he isn't complaining. But he's definitely ready to help his brother along with the joys of anal sex. Of course, he didn't expect that sweet, innocent Sam could be a little more than he could handle.





	Bliss

**Author's Note:**

> Baby's first "real" wincest. Awh.

Dean’s not sure how the hell he would up here, but here he is none the less, spread out on the bed like a starfish, licking his lips as his little brother flings his hoodie across the room. Perhaps it was the alcohol. Get enough whiskey in either of them and they’ll start talking about all kinds of embarrassing shit. Though, maybe that’s just Dean. Sam’s usually the quieter of the two, and a lot more pissy or weepy when he’s sloshed. Maybe it was the challenge. Dean’s never been one to back down from a challenge, especially when he knew he could win – and a little gay chicken with your baby brother is easy to win, especially when you’ve played with men who were way less keen on the chicken part.

Somewhere between threading his fingers in the curls at the base of Sam’s neck and Sam’s breath against his neck something changed. It could’ve been Sam that moved first, but it might’ve been Dean. Somehow, someway, their lips connected and then it was all downhill. There was a little biting, some shallow breathing, and that unmistakable glimmer of lust dancing in Sam’s eyes. Dean had asked if he was sure, he’d had to ask if Sam was sure. It wasn’t like Dean was too concerned with fucking his own brother – he’d been in the middle and on the sidelines of plenty of threesomes with twins – but Sam… Sam wasn’t as experienced as Dean was.

Now, though, Dean sits up, leaning back on his elbows as he watches Sam strip his shirt off and drops it to the floor.

“What are you looking at me like that for?” Sam asks.

“Just enjoyin’ the view.”

Sam rolls his eyes and snorts a laugh. “Whatever.”

He knee walks onto the bed, bracketing Dean’s hips with his knees. Dean is brazen in his appraisal of Sam’s body. He’s lean but the muscles in his arms and chest quiver with every breath. Dean lets one of his hands skim up Sam’s stomach, through the fine hairs on his chest and pulls him close by the back of his neck. They kiss again, Sam taking the lead this time, his tongue slipping against Deans. Dean groans, letting himself be laid back into the sheets. The springs creak beneath their weight as Sam shifts above him, tugging at the hem of Dean’s shirt until Dean lifts up a little and it’s pulled off and thrown god knows where.

Dean groans at the press of Sam’s skin against his own, their nipples brushing lightly as Sam drags his body up Deans.

“You’re sure about this?” Sam asks, “You really want to do this?”

Dean snorts. “No, I’ve just got a boner for the hell of it.”

Sam bites his shoulder and Dean shudders. “But the whole…”

“Brother thing?” Dean asks.

“Butt thing.”

Dean laughs. He doesn’t mean to, but he does. Sam pulls back and Dean has to roll over and tuck his head into the pillow so he isn’t too loud.

“Really, Sam? That’s your issue?”

Sam shoots him a grade A bitch face. “I’m serious.”

Dean takes a few deep breaths, regaining composure. He rolls back to face Sam. “Yeah, dude. I’m sure. Hey, look. If you’re not into it you can fuck me this time.”

“I was planning on it,” Sam says.

Dean can’t help his own smirk. “Sammy, you dog!” He bites at the air. Yeah, he’s a little drunk.

“I just…” Sam sighs, “I don’t want to hurt you.”

“Sam. What do you think I’ve been doing these past four years without you? Hanging out with dad on the weekends?”

“So you’ve done this before?”

“Multiple times.”

Sam mutters something that sounds a whole lot like “damn”.

“What? You disappointed?”

Sam looks away from him, a slightly darker blush creeping into his cheeks.

Dean laughs. “I could always pretend. If you’re into that kind of thing.”

“That wouldn’t be too weird, would it?”

Dean laughs again, curling up on himself, the top of his head brushing against Sam’s chest. “Dude. Look around. You're about to fuck your brother. Virgin role play aint the weirdest shit that’s going on right now.”

Sam’s body shook with a chuckle and he pushed Dean back against the bed. Dean bit his lip as Sam latched onto his neck, sucking the skin just below his ear. Dean groaned, letting his hands skim down Sam’s back, blunt nails scraping against the skin on the way back up.

“Have you ever done this before?” Dean asks, the breathlessness in his voice, not even the slightest bit put on.

Sam licked Dean’s neck, now nibbling on his earlobe. “Couple of times.” He grinds his hips down into Dean’s crotch, the bulge in his jeans pressing into his hip. Dean shudders 

“Don’t worry,” Sam purrs, “I’ll take care of you.”

“You damn well better,” Dean says, bucking his hips up.

Sam slinks down Dean’s body, delivering a sharp bite to his nipple. “Hush. You’re not supposed to be the cocky one here.”

Dean snorts. “Oh, Sammy, I’ll show you cocky.”

Sam glares at him, sucking his left nipple into his mouth, grazing his teeth against it before soothing it with his tongue. It’s almost too rough, but Dean lets his hands fall into Sam’s hair and moans anyway. Sam pulls off, completely ignoring Dean’s other nipple and drag his tongue down Dean’s stomach, nipping at his belly button before locking eyes with Dean and popping the button on his jeans.

He lifts his ass so Sam can slip his jeans and boxers off his legs before running his hands up the soft hair on Dean’s legs. His face is so close to Dean’s cock and it just with ever puff of Sam’s warm breath.

“You just gonna stare at it or...?”

Sam rolls his eyes and crawls back up Dean’s body, the skin on his stomach only incidentally brushing against Dean’s dick. Dean whines. Sam bites down on Dean’s plush lips.

“Don’t whine. You’ll get what you need eventually. Just trust me.”

Dean huffs and rolls his eyes, but Sam doesn’t see. Sam is too busy feeling him up, his large hands stroking the skin on Dean’s chest and hips, his lips teasing Dean’s open enough for Dean to try to slip his tongue into Sam’s mouth, only for Sam to pull away before he can.

Dean groans, frustrated. He wraps a leg around Sam’s calf, intent on flipping them over and getting on with it when Sam grabs his wrists and presses them into the bed, his hips pushing hard into Deans.

“Don’t even think about it,” Sam growls.

Dean’s pretty sure his brain melts, just a little bit. His body definitely does.

“You’re supposed to be the virgin here, remember. Be patient and I’ll give you what you need.”

“Yeah,” Dean gasps, his mouth feeling much drier than it did a minute ago, “how’s that?”

“Well,” Sam says, his breath soft against Dean’s lips, “I think I’ll go slow at first. Since you’re not used to it. Then, when your toes start to curl into the sheets and you can’t take it anymore when you start babbling and losing your mind, then I’m gonna give it to you fast and hard and you’re going to come screaming.”

Dean groans, rolling his head back. “Please.”

“You want that?” Sam asks.

“Don’t ask stupid questions.”

Sam bites down hard on Dean’s neck, just below his Adam’s apple. “I can get up right now and leave you here. Is that what you want, Dean?”

“No.”

“Then are you gonna be good for me?”

Dean lets out a shaking breath. “Yeah. Yeah, Sam. I’ll be good.”

“Good,” Sam says, entirely too pleased with himself. Dean’s going to make him pay for that. Eventually. Right now, though he’s hard enough to pound nails and he’s got all six-foot-four of Sam’s warm, muscular body pressing into him and he wants.

Suddenly, Sam pops up, a sudden clarity in his eyes that hasn’t been there since they started. Dean also rises up, the harsh tendrils of worry tightening in his chest. He always asks what spooked Sam when Sam speaks first.

“You have lube, right?” Sam asks, and Dean has to laugh for the third time that night.

“Bottom of my duffle bag. Far right corner, probably,” he says.

Sam bounds off the bed and towards the other double in the room. They’d started this on Sam’s bed, after all. Dean thought he was being some kind of cute, endearing asshole. Jokes on him, apparently. Not that he minds, by the way.

Sam finally finds his lube after dumping the whole damn duffle out on the bed. Dean watches the way Sam shuffles across the floor, the bulge in his jeans very noticeable. He crawls back into the bed, settling between Dean’s spread legs, squirting lube on his fingers before putting his palms on Dean’s bent knees. Dean spreads his legs as far as he can, and Sam props his ass up with a pillow he’d swiped from the other bed.

“I’m going to touch you now,” Sam says.

Dean nods. He’s breathing a little fast and his heart rate is probably through the roof by now. The second Sam’s finger touches the rim of Dean’s hole, Dean would swear he stops breathing. Sam’s gentle, maybe a little too gentle, just rubbing the sensitive furl of muscle between his legs. It’s awesome.

Dean regains control over his breathing - mostly – and watches as Sam stares intently at what he’s doing. His hair is a little damp at his temples, and his chest rises and falls with deep, measured breaths. His skin is flushed up to his neck, and he’s biting his lip. He’s so damn hot like this.

“Are you gonna, you know, get to it anytime soon?” Dean asks.

Sam glares at him between Dean’s legs, and that’s when he’s sliding into Dean’s body.

Dean gasps in way too high of a pitch and tenses immediately before falling back into the bed and forcing himself to relax. It’s not that it hurt, really, it’s just… goddamn, it’s been a while. And that first press is always something he forgets about.

“You alright?” Sam asks. There’s laughter in his voice and Dean wants to smack him.

“Yeah, yeah. ‘M fine,” Dean says.

“Are you sure? I can always stop if it’s too intense,” Sam says.

“Fuck you,” Dean snorts.

Sam slips his finger out, then presses back in, a little rough and much deeper. “Maybe. If you’re lucky.”

Dean rolls his eyes and groans, trying to focus on the feeling. It’s good, and try as he might, Dean can’t help but make it a little weird in his head. He’s getting fingered by his brother. His little brother. He watched this kid fumble his way through high school flirting and now he’s pumping in and out of Dean’s ass like it’s nothing. Good, God. All the times Dean thought about it in passing, thought about inviting Sam to a threesome, just to see what would happen. He’d always fantasized that the chick they’d be banging would want to see them kiss. That would be fucking awesome. Or maybe twins. Sam would be a little apprehensive at first, but they’d start making out with the twins and then the twins would make out with each other and then maybe he and Sam would have to keep each other occupied. It would be so dirty and wrong and terrible and so fucking great.

But nothing, damn near nothing was ever going to compare to the way Sam’s fingers felt as he thrust them in and out, scissoring and stretching and feeling around for that magic little spot inside Dean that would make him light up like a goddamn Christmas tree. Jesus, it was the fucking best.

“Glad you think so,” Sam said, chuckling against Dean’s knee.

“Fuck, did I say that out loud?” Dean groaned.

Sam’s laugh reverberated against Dean’s leg, and that’s when he found Dean’s prostate on a particularly hard press. Dean squirms, clawing the sheets beneath him, muttering swears.

“You like that?” Sam asks.

“Nofuckingshit,” Dean breathes.

Sam presses against it again, lighter this time and Dean whimpers. He backs off them, lazily going about his business. Dean’s panting, throwing his head from side to side, whining.

“Come on, Sam, I’m ready,” Dean says.

Sam just hums, tugging at Dean’s rim when he pulls his fingers out.

“Saaam,” Dean whines.

Sam isn’t deterred, instead, he goes much slower. Dean shudders.

“You’re driving me fucking crazy down there, Sam. Good god, I’m good. Get your dick out and fuck me already.”

Sam sits up on his haunches, pulling his fingers out for a final time before wiping them on the bed. “You’re sure? I’m kinda big.”

Dean snorts. “Sam, come on. I can take it.”

“You’re sure?”

“Fuck. Yes.”

Sam shakes his head but acquiesces, hastily undoing his pants and slipping off the bed. He shucks his jeans to the floor, followed by his boxers, and Dean gasps.

Sam wasn’t lying. Nope. Not in the slightest. He’s big, both in length and girth. Dean’s eyes trail from Sam’s cock to his face, then back to his cock again.

“I told you,” Sam says.

“That’s not gonna fit,” Dean says, a little breathless.

Sam slides back onto the bed, setting himself up between Dean’s knees. “I thought you said you could take it.” He’s smirking. Fucking asshole.

“Well yeah, but that’s before…” Dean gestures vaguely at the space between them.

Sam, completely unfazed, squirts lube right onto his dick and strokes himself. “I’ll make it fit.”

Dean gulps. “Yeah, okay.”

“Lay back,” Sam says, pushing Dean’s shoulder with his fingertips. Dean falls backward. “And relax. No need to be nervous.”

Nervous is… okay, that’s a little accurate. Dean hasn’t slept with anyone with a cock like that since… Rhonda probably. She had a huge dick. But this… this was Sam. His little brother who was apparently hung like a goddamn horse and totally intent on drilling him into the mattress. Sure, he was nervous, but he was also thrilled as fuck and really turned on and maybe a little overwhelmed. He was a lot of things.

Dean’s focusing on his breathing now. The head of Sam’s dick is flush against his rim and Dean’s whole body is buzzing. Sam’s stroking his thigh, and Dean shuts his eyes. Sam starts pushing.

“Fuck,” Dean mutters. He’s breathing a little too hard and a little too loud. He’s not scared, just excited.

Sam pushes in steadily, and if he looked big outside he feels enormous. Dean wants to thrash around. He wants to moan and scream and claw Sam’s back until he’s drawing blood. Fuck. It’s so good.

“Relax, Dean,” Sam says. His voice is soft as he leans over Dean’s stomach.

“Can’t,” Dean says through gritted teeth.

“I can stop if –“

“Don’t you fucking dare,” Dean moans. “God, you’re so...” Dean’s eyes flutter open and he finds Sam hovering over him. There’s a smile on his face and pure mischief in his eyes. “You’re such a fucker,” Dean laughs.

Sam rolls his eyes and continues pushing in. He stills when he’s finally as far in as he’s willing to go and he rests his forehead against Dean’s shoulder. Dean runs his fingers through Sam’s hair, and they breathe together. Sam raises up on his elbows and begins rocking in and out slowly. It’s nice at first and gives Dean plenty of time to adjust. It stings a bit, but he adjusts, and soon he’s making soft little noises somewhere between groans and whimpers.

Sam doesn’t speed up or go faster when Dean starts to claw at his back or bite on his neck. He’s going to have hickeys for weeks, but it’s not like Dean gives a fuck. Apparently, Sam doesn’t either.

“Sam,” Dean sighs, “Sam, faster.”

Sam grunts and shakes his head.

“Come on, Sam, I can take it.”

Sam just shakes his head. “No, not yet.”

Dean whines and kicks his heels into Sam’s ass. Sam stops moving altogether and shoots him a bitchface.

“Come. On. Fuck me,” Dean whines.

Sam circles his hips and Dean gasps. “No.”

“Please.”

Sam draws back and slides in twice then stills. “How bad do you want it?”

“Goddammit! Please. Fuck, Sam. Give it to me. I need it.”

“Beg.”

Dean whines like he’s in pain. “Please, Sam. Please just give it to me. Fuck me like I know you can. Please, babe.”

Sam pulls back and thrusts in hard. Dean howls.

Sam doesn’t let up then. He clutches around Dean’s shoulders and drives in and out, hard and fast and Dean’s moaning loud enough that he’s sure everyone in the motel can hear them. He’s got his legs wrapped around Sam’s calves, nails digging into his shoulder blades.

“Fuck. Fuck. Fuckfuckfuck,” Dean’s gasping and groaning.

“You like that?” Sam taunts, “You like getting fucked by your baby brother?”

Dean’s moans sound foreign and high pitched to his own ears. “Yes. God, yes. Sammy. Sammy don’t stop.”

“You sure? I could you know. I could just pull out right now.”

“No!” Dean bites down into Sam’s shoulder. It’s going to leave marks.

“Tell me you love it.”

“Fuck, Sam, I love it. God. Please don’t stop. Fucking please.” Dean starts screaming. It’s like every nerve in his body is alive, all singing and screaming and desperate to never let this end. He’s wanted this for years and he wants it to last for years.

Dean’s breathing starts up in harsh pants. He’s not screaming anymore, but his body is. He’s on the edge, riding that high that he knows is going to shatter him if it doesn’t literally kill him in the process. Sam is grunting now, too, his rhythm slipping.

Dean’s practically hyperventilating when it happens. That warm in his core, his groin, and he comes in a scream that starts silent and ends anything but. His head falls back against the pillow and he’s loose, limp, and floating somewhere else as Sam finishes above him, curling in on himself and Dean.

Dean’s pretty sure he’s ascended to some higher level of consciousness. He’s been fucked straight out of his body and into the astral plane. That’s it. He’s ruined.

“Dean?” Sam’s voice comes from his left and Dean turns his head lazily. “Are you okay.”

Dean smiles. “I am so fucking good.”

“I didn’t hurt you, did I?”

Dean rolls his eyes. “The opposite.”

“Oh. Good.”

Sam’s biting his lip, scooting closer but not touching.

“Dude, if you wanna cuddle or whatever, go for it. I’m goo right now, so don’t expect much from me though.”

Sam shakes his head and pulls Dean close. “You’re an ass.”

Dean doesn’t even respond. He just presses as close to Sam as his tired body will allow.

He’s not sure how he got here, but fuck if he’d be anywhere else.

 

 

 

**Author's Note:**

> Comments and kudos make me very happy. 
> 
> Come talk to me on [tumblr!](http://marymotherofmonsters.tumblr.com/)


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